CA2291215C - Nouveaux catalyseurs a action retardee pour mousse de support de tapis et mousse expansee a l'air - Google Patents

Nouveaux catalyseurs a action retardee pour mousse de support de tapis et mousse expansee a l'air Download PDF

Info

Publication number: CA2291215C
Authority: CA; Canada
Prior art keywords: weight; reaction mixture; air; polyol; diphenylmethane diisocyanate
Prior art date: 1998-12-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002291215A

Other languages

English (en)

Other versions

CA2291215A1 (fr

Inventor

James W. Rosthauser

Hartmut Nefzger

Robert L. Cline

Gerard C. Erhart

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Corp

Original Assignee

Bayer Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-12-02

Filing date

1999-11-29

Publication date

2009-10-20

1999-11-29 Application filed by Bayer Corp filed Critical Bayer Corp

2000-06-02 Publication of CA2291215A1 publication Critical patent/CA2291215A1/fr

2009-10-20 Application granted granted Critical

2009-10-20 Publication of CA2291215C publication Critical patent/CA2291215C/fr

2019-11-29 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims abstract description 76
239000006260 foam Substances 0.000 title claims abstract description 26
230000009471 action Effects 0.000 title description 12
230000003111 delayed effect Effects 0.000 title description 12
239000000203 mixture Substances 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 45
230000008569 process Effects 0.000 claims abstract description 41
229920005862 polyol Polymers 0.000 claims abstract description 35
150000003077 polyols Chemical class 0.000 claims abstract description 35
239000004814 polyurethane Substances 0.000 claims abstract description 26
229920002635 polyurethane Polymers 0.000 claims abstract description 26
239000005056 polyisocyanate Substances 0.000 claims abstract description 25
229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
239000000758 substrate Substances 0.000 claims abstract description 24
239000011541 reaction mixture Substances 0.000 claims abstract description 23
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
238000002156 mixing Methods 0.000 claims abstract description 15
238000004519 manufacturing process Methods 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000004122 cyclic group Chemical group 0.000 claims abstract description 9
-1 polymethylene Polymers 0.000 claims description 58
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 33
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 16
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 11
229920000570 polyether Polymers 0.000 claims description 11
229920005903 polyol mixture Polymers 0.000 claims description 11
239000000178 monomer Substances 0.000 claims description 9
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 7
239000004970 Chain extender Substances 0.000 claims description 6
239000004721 Polyphenylene oxide Substances 0.000 claims description 6
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 6
239000004604 Blowing Agent Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
ZDCQVWDLQGHLKR-UHFFFAOYSA-N 2,2,4,4-tetrabutyl-1,3,2,4-dithiadistannetane Chemical compound CCCC[Sn]1(CCCC)S[Sn](CCCC)(CCCC)S1 ZDCQVWDLQGHLKR-UHFFFAOYSA-N 0.000 claims description 4
KLKYIDMJFKMOJH-UHFFFAOYSA-N 2,2,4,4-tetradodecyl-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCCCCCC[Sn]1(CCCCCCCCCCCC)S[Sn](CCCCCCCCCCCC)(CCCCCCCCCCCC)S1 KLKYIDMJFKMOJH-UHFFFAOYSA-N 0.000 claims description 4
LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 3
JAASHQKSLWPTQV-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3,2,4-dithiadistannetane Chemical compound C[Sn]1(C)S[Sn](C)(C)S1 JAASHQKSLWPTQV-UHFFFAOYSA-N 0.000 claims description 3
AGYDQNFZBRUJMN-UHFFFAOYSA-N 2,2,4,4-tetraoctyl-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCC[Sn]1(CCCCCCCC)S[Sn](CCCCCCCC)(CCCCCCCC)S1 AGYDQNFZBRUJMN-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 3
229920000638 styrene acrylonitrile Polymers 0.000 claims description 2
239000011369 resultant mixture Substances 0.000 claims 2
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
239000012948 isocyanate Substances 0.000 description 26
150000002513 isocyanates Chemical class 0.000 description 24
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
150000001875 compounds Chemical class 0.000 description 13
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
235000019645 odor Nutrition 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
150000004072 triols Chemical class 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XIYCUDKBCGXXKZ-UHFFFAOYSA-N 2,2,4,4-tetracyclohexyl-1,3,2,4-dithiadistannetane Chemical compound C1CCCCC1[Sn]1(C2CCCCC2)S[Sn](C2CCCCC2)(C2CCCCC2)S1 XIYCUDKBCGXXKZ-UHFFFAOYSA-N 0.000 description 3
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
SPIUEOWNLJQKJK-UHFFFAOYSA-J 2-sulfanylacetate tin(4+) Chemical class [Sn+4].[O-]C(=O)CS.[O-]C(=O)CS.[O-]C(=O)CS.[O-]C(=O)CS SPIUEOWNLJQKJK-UHFFFAOYSA-J 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
229940035437 1,3-propanediol Drugs 0.000 description 2
MIUZAZPVUJOFPJ-UHFFFAOYSA-N 2,2,4,4-tetra(cyclooctyl)-1,3,2,4-dithiadistannetane Chemical compound C1CCCCCCC1[Sn]1(C2CCCCCCC2)S[Sn](C2CCCCCCC2)(C2CCCCCCC2)S1 MIUZAZPVUJOFPJ-UHFFFAOYSA-N 0.000 description 2
AXBDFKAZFVYZNB-UHFFFAOYSA-N 2,2,4,4-tetra(nonyl)-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCCC[Sn]1(CCCCCCCCC)S[Sn](CCCCCCCCC)(CCCCCCCCC)S1 AXBDFKAZFVYZNB-UHFFFAOYSA-N 0.000 description 2
IUNBBZUATUGAQF-UHFFFAOYSA-N 2,2,4,4-tetra(pentadecyl)-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCCCCCCCCC[Sn]1(CCCCCCCCCCCCCCC)S[Sn](CCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCC)S1 IUNBBZUATUGAQF-UHFFFAOYSA-N 0.000 description 2
GCRGUOLSZKIGTK-UHFFFAOYSA-N 2,2,4,4-tetra(tridecyl)-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCCCCCCC[Sn]1(CCCCCCCCCCCCC)S[Sn](CCCCCCCCCCCCC)(CCCCCCCCCCCCC)S1 GCRGUOLSZKIGTK-UHFFFAOYSA-N 0.000 description 2
QFAXIVNSHMKNQF-UHFFFAOYSA-N 2,2,4,4-tetracyclopentyl-1,3,2,4-dithiadistannetane Chemical compound C1CCCC1[Sn]1(C2CCCC2)S[Sn](C2CCCC2)(C2CCCC2)S1 QFAXIVNSHMKNQF-UHFFFAOYSA-N 0.000 description 2
AVPHTCVLOBHQMW-UHFFFAOYSA-N 2,2,4,4-tetraheptyl-1,3,2,4-dithiadistannetane Chemical compound CCCCCCC[Sn]1(CCCCCCC)S[Sn](CCCCCCC)(CCCCCCC)S1 AVPHTCVLOBHQMW-UHFFFAOYSA-N 0.000 description 2
WGQMIPGMVNBVAG-UHFFFAOYSA-N 2,2,4,4-tetrahexadecyl-1,3,2,4-dithiadistannetane Chemical compound CCCCCCCCCCCCCCCC[Sn]1(CCCCCCCCCCCCCCCC)S[Sn](CCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCC)S1 WGQMIPGMVNBVAG-UHFFFAOYSA-N 0.000 description 2
BXOKDNJTOMKOAH-UHFFFAOYSA-N 2,2,4,4-tetrahexyl-1,3,2,4-dithiadistannetane Chemical compound CCCCCC[Sn]1(CCCCCC)S[Sn](CCCCCC)(CCCCCC)S1 BXOKDNJTOMKOAH-UHFFFAOYSA-N 0.000 description 2
NDZVWJXBZAZYGU-UHFFFAOYSA-N 2,2,4,4-tetrapentyl-1,3,2,4-dithiadistannetane Chemical compound CCCCC[Sn]1(CCCCC)S[Sn](CCCCC)(CCCCC)S1 NDZVWJXBZAZYGU-UHFFFAOYSA-N 0.000 description 2
JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OWRNLGZKEZSHGO-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-hydroxypropoxy)propoxy]propoxy]propoxy]propoxy]propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)COC(C)COC(C)COC(C)COC(C)CO OWRNLGZKEZSHGO-UHFFFAOYSA-N 0.000 description 2
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
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240000000491 Corchorus aestuans Species 0.000 description 2
235000011777 Corchorus aestuans Nutrition 0.000 description 2
235000010862 Corchorus capsularis Nutrition 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
239000000654 additive Substances 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
239000000835 fiber Substances 0.000 description 2
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012528 membrane Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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150000002924 oxiranes Chemical class 0.000 description 2
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229920000166 polytrimethylene carbonate Polymers 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
150000003384 small molecules Chemical class 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
239000012974 tin catalyst Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
150000004684 trihydrates Chemical class 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Chemical group CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
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KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
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LHOBKFFUEUQRQX-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,5-diol Chemical compound OCC(C)CC(C)(C)CO LHOBKFFUEUQRQX-UHFFFAOYSA-N 0.000 description 1
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BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
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IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000016976 Quercus macrolepis Nutrition 0.000 description 1
244000305267 Quercus macrolepis Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229920001893 acrylonitrile styrene Polymers 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009408 flooring Methods 0.000 description 1
239000010881 fly ash Substances 0.000 description 1
239000004872 foam stabilizing agent Substances 0.000 description 1
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Chemical group CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
- C08G18/8019—Masked aromatic polyisocyanates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Inorganic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)

CA002291215A 1998-12-02 1999-11-29 Nouveaux catalyseurs a action retardee pour mousse de support de tapis et mousse expansee a l'air Expired - Fee Related CA2291215C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US20387598A	1998-12-02	1998-12-02
US09/203,875		1998-12-02
US09/326,831		1999-06-07
US09/326,831 US6140381A (en)	1998-12-02	1999-06-07	Delayed action catalysts for carpet backing and air frothed foam

Publications (2)

Publication Number	Publication Date
CA2291215A1 CA2291215A1 (fr)	2000-06-02
CA2291215C true CA2291215C (fr)	2009-10-20

Family

ID=31890891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002291215A Expired - Fee Related CA2291215C (fr)	1998-12-02	1999-11-29	Nouveaux catalyseurs a action retardee pour mousse de support de tapis et mousse expansee a l'air

Country Status (2)

Country	Link
US (1)	US6140381A (fr)
CA (1)	CA2291215C (fr)

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US7763341B2 (en)	2004-01-23	2010-07-27	Century-Board Usa, Llc	Filled polymer composite and synthetic building material compositions
EP1776216A4 (fr)	2004-06-24	2009-04-08	Century Board Usa Llc	Installation de fabrication en continu d'articles tridimensionnels en mousse
US7794224B2 (en)	2004-09-28	2010-09-14	Woodbridge Corporation	Apparatus for the continuous production of plastic composites
AU2005299518B2 (en) *	2004-10-25	2011-09-22	Dow Global Technologies Llc	Polyurethane carpet backings made using hydroxymethylated polyester polyols
US20070225419A1 (en)	2006-03-24	2007-09-27	Century-Board Usa, Llc	Polyurethane composite materials
BRPI0709479B1 (pt) *	2006-04-07	2018-05-29	Dow Global Technologies Inc.	Processo para manufaturar produtos de forro para carpetes e processo para formar um poliol formulado
AU2010201270A1 (en) *	2009-04-07	2010-10-21	Plasan Sasa Ltd.	Safety apparatus for providing protection against an explosion and vehicle comprising same
US9481759B2 (en)	2009-08-14	2016-11-01	Boral Ip Holdings Llc	Polyurethanes derived from highly reactive reactants and coal ash
US8846776B2 (en)	2009-08-14	2014-09-30	Boral Ip Holdings Llc	Filled polyurethane composites and methods of making same
WO2013052732A1 (fr)	2011-10-07	2013-04-11	Boral Industries Inc.	Composites de polymère inorganique/polymère organique et procédés pour les préparer
BR112014015221A2 (pt)	2011-12-20	2017-06-13	Bayer Intellectual Property Gmbh	polímeros de hidroxi-amino e processos para a sua preparação
DE102012106561A1 (de)	2012-07-19	2014-02-20	Benecke-Kaliko Ag	Verbundschichtmaterial, Verfahren zu dessen Herstellung und Verwendung
DE102012106559A1 (de)	2012-07-19	2014-02-20	Benecke-Kaliko Ag	Verbundschichtmaterial, Verfahren zu dessen Herstellung
WO2014168633A1 (fr)	2013-04-12	2014-10-16	Boral Ip Holdings (Australia) Pty Limited	Composites formés à partir d'une charge absorbante et d'un polyuréthane
WO2016018226A1 (fr)	2014-07-28	2016-02-04	Crocco Guy	Utilisation d'agents réfrigérants évaporatifs pour fabriquer des composites de polyuréthane chargés
WO2016022103A1 (fr)	2014-08-05	2016-02-11	Amitabha Kumar	Composites polymères chargés comprenant des fibres de courte longueur
WO2016118141A1 (fr)	2015-01-22	2016-07-28	Boral Ip Holdings (Australia) Pty Limited	Composites de polyuréthanne hautement chargés
US10030126B2 (en)	2015-06-05	2018-07-24	Boral Ip Holdings (Australia) Pty Limited	Filled polyurethane composites with lightweight fillers
US20170267585A1 (en)	2015-11-12	2017-09-21	Amitabha Kumar	Filled polyurethane composites with size-graded fillers
EP4063420A1 (fr)	2021-03-24	2022-09-28	Evonik Operations GmbH	Procédés, compositions et produits de polyuréthane présentant un catalyseur thermolatent à base d'amine

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US3813424A (en) *	1971-06-04	1974-05-28	Kureha Chemical Ind Co Ltd	Process of the manufacture of dialkyltin oxide
US4087412A (en) *	1976-05-11	1978-05-02	Minnesota Mining And Manufacturing Company	Organotin catalyst system for isocyanate reactions
US4549945A (en) *	1984-01-11	1985-10-29	Phillips Petroleum Company	UV Cured polyurethanes using organotin promoters
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US5646195A (en) *	1995-03-07	1997-07-08	The Dow Chemical Company	Catalyst for polyurethane carpet backings and carpets prepared therewith
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1999
- 1999-06-07 US US09/326,831 patent/US6140381A/en not_active Expired - Fee Related
- 1999-11-29 CA CA002291215A patent/CA2291215C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2291215A1 (fr)	2000-06-02
US6140381A (en)	2000-10-31

Legal Events

Date	Code	Title	Description
2004-10-21	EEER	Examination request
2012-11-29	MKLA	Lapsed
2013-01-10	MKLA	Lapsed	Effective date: 20121129

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JP2020517484A (ja)	2020-06-18	エラストマー複合材ポリウレタンスキン
CN105073812A (zh)	2015-11-18	将粘合剂组合物施加至木质纤维基材的方法
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